Process for producing arylsulfur pentafluorides

Abstract

Novel processes for preparing arylsulfur pentafluorides are disclosed. Processes include reacting at least one aryl sulfur compound with a halogen and a fluoro salt to form an arylsulfur halotetrafluoride. The arylsulfur halotetrafluoride is reacted with a fluoride source to form a target arylsulfur pentafluoride.

I claim: 
     
       1. A process for preparing an arylsulfur pentafluoride having a formula (I): 
       
         
           
           
               
               
           
         
       
       the process comprising:
 reacting an arylsulfur trifluoride having a formula (V): 
 
       
         
           
           
               
               
           
         
       
       with a halogen selected from the group consisting of chlorine, bromine, iodine, and interhalogens and a fluoro salt having a formula (III) to form an arylsulfur halotetrafluoride having a formula (IV):
   M + F −   (III)
 
 
       
         
           
           
               
               
           
         
       
       and reacting the obtained arylsulfur halotetrafluoride with a fluoride source to form the arylsulfur pentafluoride;
 in which: R 1 , R 2 , R 3 , R 4 , and R 5  each is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or unsubstituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted acyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted alkanesulfonyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, or a SF 5  group; 
 M is a metal atom, an ammonium moiety, or a phosphonium moiety; 
 X is a chlorine atom, a bromine atom, or an iodine atom; and wherein the solvent is not fluorinated by said process. 
 
     
     
       2. The process of  claim 1  wherein the halogen reacted with the arylsulfur trifluoride is chlorine (Cl 2 ). 
     
     
       3. The process of  claim 1  wherein the fluoro salt having a formula (III) is an alkali metal fluoride. 
     
     
       4. The process of  claim 1  wherein the fluoride source is at least one member selected from a group consisting of fluorides of typical elements in the Periodic Table, fluorides of transition elements in the Periodic Table, and mixture or compounds between or among these fluorides of typical elements and/or transition elements, as well as mixtures, salts, or complexes of these fluorides with organic molecules. 
     
     
       5. The process of  claim 1 , further comprising the reaction of the obtained arylsulfur halotetrafluoride with a fluoride source being performed in the presence of a halogen selected from the group of chlorine, bromine, iodine, and interhalogens to form the arylsulfur pentafluoride. 
     
     
       6. A process for preparing an arylsulfur halotetrafluoride having a formula (IV): 
       
         
           
           
               
               
           
         
       
       the process comprising;
 reacting an arylsulfur trifluoride having a formula (V); 
 
       
         
           
           
               
               
           
         
       
       with a halogen selected from the group consisting of chlorine, bromine, iodine, and interhalogens and a fluoro salt having a formula (III) to form the arylsulfur halotetrafluoride:
   M + F −   (III)
 
 in which: R 1 , R 2 , R 3 , R 4 , and R 5  each is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or unsubstituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted acyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted alkanesulfonyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, or a SF 5  group; 
 M is a metal atom, an ammonium moiety, or a phosphonium moiety; and 
 X is a chlorine atom, a bromine atom, or an iodine atom; and wherein the solvent is not fluorinated by said process. 
 
     
     
       7. The process of  claim 6  wherein the halogen reacted with the arylsulfur trifluoride is chlorine (Cl 2 ). 
     
     
       8. The process of  claim 6  wherein the fluoro salt having a formula (III) is an alkali metal fluoride.